Process for controlling undesired vegetation

ABSTRACT

A process for controlling undesired vegetation, in particular, a process for controlling undesired vegetation without damaging crop plants using substituted esters of N-phenylaminoacrylic acid.

United States Patent Scheuermann et al.

[ 3,656,932 [451 Apr. 18, 1972 PROCESS FOR CONTROLLING UNDESIRED VEGETATION Inventors: Horst Scheuermann, Ludwigshafen/ Rhine;

Adolf Fischer, Mutterstadt/Pfalz, both of Germany Assignee: Badische Anilin- & Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhine and Rhineland-Pfalz, Germany Filed: Sept. 6, 1968 Appl. No.2 758,103

Foreign Application Priority Data Sept. 15, 1967 Germany ..P 16 42 231.4

U.S. Cl ..7l/105, 71/103, 71/104 Int. Cl. ..A01n 9/20 Field of Search ..7l/105, 103

Plaisted Growth Suppression by a Cyanocinamic Acids" Contributions from Boyce Thompson lnstitute Vol. 18. (1955),' 23l- 242.

Primary Examiner-Lewis Gotts Assistant Examiner-Catherine L. Mills Attorney-Marzall, Johnston, Cook & Root [5 7] ABSTRACT A process for controlling undesired vegetation, in particular, a process for controlling undesired vegetation without damaging crop plants using substituted esters of N-phenylaminoacrylic acid.

6 Claims, No Drawings in which X andY denote nitrile radicals, acetyl radicals or radicals -COOR", wherein R" denotes a lower aliphatic radical, R denotes hydrogen, a lower aliphatic radical or an aralkyl radical and R denotes halogen, in particular chlorine, or bromine, a lower saturated or unsaturated aliphaticradical, preferably a methyl or ethyl radical, or a haloalkyl radical, such as a trichloromethyl or trifluoromethyl radical, or an alkoxy radical, preferably a methoxy or ethoxy radical, a cyano or thiocyano group, a carboxyl group which may be esterified, a nitro group, a sulfonamide group which may be N-alkylated or an acylated amino group and n denotes an integer from to 5, wherein should n be greater than 1 the radicals R may be identical or different, have a good herbicidal action.

The compounds to be used in accordance with this invention may be produced by reacting N-substituted formanilide chlorides with methylene-active compounds such as alkyl cyanoacetatcs, dialkyl malonates, malononitrile or acetoacetate (Chem. Ber., 94, 2285( 1961)).

However, in accordance with J. Am. Chem. Soc., 68, 1253 (1946) or J.Am. Chem. Soc., 82, 718 (l 960),.these compounds may also be produced by reacting alkyl ethoxymethylene cyanoacetates, ethoxymethylene malononitrile dialkyl ethoxymethylene malonates or ethoxymethylene acetoacetates with appropriately substituted aniline derivatives.

For example, ethyl /3-(N-phenyl-N-methyl)-amino-a-cyano acrylate may be prepared by the following method: 40.5 parts of N-methyl-formanilide'is added within 20 minutes at 0 C to a solution of 33 parts by weight of phosgene in 150 parts of toluene. After stirring for 2 hours at room temperature (20 C), 33.9 parts of ethyl cyanoacetate and 60.6 parts of triethylamine are added to the mixture and the whole is stirred at 60 to 70 C for a further 2 hours. After cooling and suction filteringthe precipitated triethylamine hydrochloride, the filtrate is concentrated in vacuo. 52 parts (75 percent of the theory) of the acrylic acid derivative having a melting point of 102 to 104 is obtained.

The active ingredients may be made units emulsions or dispersions by means of emulsifiers and dispersants and adding solvents, e. g., mineral oil fractions, such as coal tar oils or diesel oil or vegetable oils or cyclic hydrocarbons or inert material such as diatomite or kaolin, and, after the addition of water, may be used as herbicides. It is possible to use the herbicides as granules as well as to mix them with fertilizers, other herbicides, fungicides or insecticides.

EXAMPLE I acrylate (I), and, for comparison, with 2 kg/ha of the potassium salt of 2-methyl-4-chlorophenoxyacetic acid (II), this amountof both active ingredients being dissolved or dispersed in 500 liters of water per hectare. After 3 to 4 weeks the ethyl results were determined:

Active ingredient I ll Crop plants: Indian corn 0-10 40 Rice 0 20 Cotton 10 Unwanted plants: Wild mustard -100 White goosefoot 80 90-100 Small nettle lOO 90-l00 Annual meadow grass 80 10 Slender foxtail 80 10-20' Barnyard grass 90 0-10 0 no damage, total destruction EXAMPLE 2 An agricultural cultivated area overgrown with small nettle (Urtica urens), white goosefoot (Chenopodium album), wild mustard (Sinapis arvensis), common chickweed (Slellaria media), annualmeadow grass (Poa annua), barnyard grass (Echinochloa crus-galli) and slender foxtail (Alopecurus myosuroides), was treated at agrowth height of 2 to 8 cm with 5 kg/ha of the active ingredient ethyl B-(Nphenyl-N-methyl)- amino-a-cyano acrylate (I), dispersed in 600 liters of water per hectare.

After 3 to 4 days the above-mentioned weeds and weed grasses started to wither, and,after 2 to 3 weeks, all weeds and weed grasses had been almost completely destroyed. The area could be cultivated again.

EXAMPLE 3 Plastic pots having a diameter of 8 cm. were filled with loamy sandy oil and then sown with seeds of Indian corn (Zea mays), rice (Oryza sativa), cotton (Gassypiam sp.), potatoes (Solanum tuberosum), wild mustard (Sinap is arvensis), small nettle (Urtica urens) and barnyard grass (Echinochloa crusethyl ,B-(N-p-methylphenyl)-amino-a-cyano acrylate ethyl /3-(N-3,4-dichlorophenyl)-amino-a-cyano acrylate ethyl B-(N-2,4-dichlorophenyl)-amino-a-cyano acrylate ethyl B-( N-phenyl)-amino-a-cyano acrylate ethyl B-(N-m-chlorophenyl)-amino-a-carbethoxy acrylate B-( N-m-trifluoromethylphenyl)-amino-a-carbethoxy acrylate 1 ethyl ,B-( N-o-cyanophenyl)-amino-a-carbethoxy acrylate ethyl B-( N-phenyl)-amino-a-carbethoxy acrylate ethyl B-(N-p-bromophenyl)-amino-a-carbethoxy acrylate ethyl B-(N-2,4,5-trichlorophenyl)-amino-a-carbethoxy acrylate ethyl B-( N-p-methylphenyl)-amino-a-acetyl acrylate ethyl fl-( N-m-chlorophenyl)-amino-a-acetyl acrylate ethyl B-(N-m-trifluoromethylphenyl)-amino-a-acetyl acrylate ethyl B-(N-o-cyanophenyl)-amino-a-acetyl acrylate ethyl fl-( N-phenyl)-amino-a-acetyl acrylate acrylate.

3. A process as claimed in claim 1, wherein said selective herbicide is ethyl fl-(N-p-methylphenyl-N-methyl)-amino-acyano acrylate.

4. A process as claimed in claim 1, wherein said selective herbicide is ethyl B-(N-dichlorophenyl)-amino-a-cyano acrylate.

5. A process as claimed in claim 1, wherein said selective herbicide is ethyl /3-(N-dichlorophenyl)-amino-a-cyano acrylate.

6. A process as claimed in claim 1, wherein said selective herbicide is ethyl ,B-(N-phenyl)-amino-a-cyano acrylate.

UNITED STATES PATENT OFFICE Patent No. 3 6'56, 932 D d April 18,- 1972 Inventor(s) Horst Scheuermann and Adolf Fischer It is certified that error appears in the above-identified patent and that said Let ters Patentare hereby corrected as shown below:

First page, right-hand column, "a Cyanocinamic" should read 8. Cyanocinnamic- Column 1, line 8, "undersired" should reed --undesired-.

Column 2, the table under "11'', "1r" should read --90--.

Column 3, line 8 "60" should read Q--.

Column 3, line 9, "dichlorophenyl" should read --p-methylphenyl-- (applicants' error).

Column 4, line 9, "dichlorophenyl" should read --pmethylphenyl-- (applicants' error) Y Signed and sealed this 3rd day of December 197A.

(REAL) Attest:

MCCOY M. GIBSON JR. 6. MARSHALL DANN Attesting Officer Commissioner of Patents FORM P0405) (19-59) I uscoMM-Dc eoa7e4=e9 U.5. GOVERNMENT PRINTING OFFIC E I '99 l56-5J CERTIFICATE OF CORRECTION l 

2. A process as claimed in claim 1, wherein said selective herbicide is ethyl Beta -(N-phenyl-N-methyl)-amino- Alpha -cyano acrylate.
 3. A process as claimed in claim 1, wherein said selective herbicide is ethyl Beta -(N-p-methylphenyl-N-methyl)-amino-Alpha -cyano acrylate.
 4. A process as claimed in claim 1, wherein said selective herbicide is ethyl Beta -(N-dichlorophenyl)-amino- Alpha -cyano acrylate.
 5. A process as claimed in claim 1, wherein said selective herbicide is ethyl Beta -(N-dichlorophenyl)-amino- Alpha -cyano acrylate.
 6. A process as claimed in claim 1, wherein said selective herbicide is ethyl Beta -(N-phenyl)-amino- Alpha -cyano acrylate. 